Ammonia → HCID 57659335, compound

HRID 1403222Notes

Reaction equation

HRID 1403222 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([C:8]2[NH:12][C:11]([C:13]3[CH:18]=[C:17]([Cl:19])[CH:16]=[CH:15][C:14]=3[CH3:20])=[C:10]([C:21]([OH:23])=O)[CH:9]=2)[CH:5]=[CH:4][N:3]=1.CC[N:26](C(C)C)C(C)C.CCN=C=NCCCN(C)C.Cl.C1C=CC2N(O)N=NC=2C=1.N>CN(C=O)C.O>[NH2:1][C:2]1[N:7]=[C:6]([C:8]2[NH:12][C:11]([C:13]3[CH:18]=[C:17]([Cl:19])[CH:16]=[CH:15][C:14]=3[CH3:20])=[C:10]([C:21]([NH2:26])=[O:23])[CH:9]=2)[CH:5]=[CH:4][N:3]=1

Participants

8

Reactant 5

HCID 222AmmoniaHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 70979820HCID 70979820, compound

Product 1

HCID 57659335HCID 57659335, compoundYield 82%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 5-(2-amino-pyrimidin-4-yl)-2-(5-chloro-2-methyl-phenyl)-1H-pyrrole-3-carboxylic acid (11.62 g, 30.4 mmol) in DMF (100 mL) and DIPEA (21.2 mL, 121.6 mmol) was stirred at 0° C. EDCl (11.64 g, 60.8 mmol) and HOBT.NH3 (9.38 g, 60.8 mmol) were added and the reaction mixture was stirred for 3 h at room temperature. The mixture was diluted with water and the resultant precipitate was collected by filtration to afford the title compound (8.17 g, 82%).

Workup

  1. filtrationthe resultant precipitate was collected by filtration

Sources & evidence

ORD record
ord-bd75ed597ad548789932f22841c2960f
Source dataset
uspto-grants-2014_12
Patent number
US08912200B2

Reaction notes

Loading…